Patent GB-1195652-A (GB)
Title: Anionic Surface-Active Agents and Cosmetic Compositions Containing them
Inventor: VANLERBERGHE GUY
IPC: C07C317/00
Filed: 1968-08-07
Abstract: 1,195,652. Anionic surface-active agents. L'OREAL. 7 Aug., 1968 [7 Aug., 1967], No. 37644/68. Heading C2C. [Also in Divisions C5 and D1] Novel anionic chemical compounds having surface activity and having the Formula (I): in which R is an aliphatic alkyl or alkenyl radical having from 8 to 22 carbon atoms or an alkyl-aryl radical having from 12 to 22 carbon atoms, X and X<SP>1</SP> may be identical or different and represent oxygen, sulphur or the sulphoxide grouping, A represents an ethylene, propylene or butylene radical, A<SP>1</SP> represents a radical -C 2 H 3 (CH 2 OH)- or -CH 2 CHOH-CH 2 -, A<SP>11</SP> represents a radical -CH 2 CHOH-CH 2 -, a radical -CH 2 CH 2 CH- or a radical -CH 2 CH(CH 3 )-, at least one of the radicals A<SP>1</SP> and A<SP>11</SP> being a hydroxyalkylene radical, respectively, as defined above, each of m and n, which may be the same or different, represents a statistical average value from 0 to 10 inclusive, and R<SP>1</SP> represents a H atom or a methyl or ethyl radical, it being understood that if m and n are simultaneously nought, X<SP>1</SP> is necessarily the sulphoxide grouping, are prepared by:-(a) when X<SP>1</SP> is the sulphoxide grouping, treating a compound of the Formula (I) having a thioether bond with hydrogen peroxide in the presence of a carboxylic acid and preferably acetic acid (about 1 or 2% of the total dry extract) at a temperature between 0‹ and 50‹ C.; (b) when X<SP>1</SP> is an oxygen atom, reacting a polyether alcohol alcoholate of the formula in which R, X, A, A<SP>11</SP>, m and n are as defined above and A<SP>111</SP> is identical to A<SP>1</SP> or may represent radicals -C 2 H 3 (CH 2 Cl)- or -C 2 H 3 - (CH 2 Br)- and M is an alkali metal, with a salt of a haloalkanecarboxylic acid of the formula where R<SP>1</SP> is as defined above and M<SP>1</SP> is an alkali or alkaline earth metal and Y represents a halogen atom, preferably bromine or chlorine; or when A<SP>1</SP> represents a group -C 2 H 3 (CH 2 OH)- and A<SP>11</SP> represents a group -CH 2 CHOHCH 2 -, reacting a glycidyl ether of the Formula (VIII): with a haloalkane carboxylic acid of the formula where R, X, A, R<SP>1</SP>, m and n are as defined above and Y and Z, which may be the same or different, represent a halogen atom and the product is treated with an alkali-metal hydroxide, and optionally liberating the free acid from its salt by means of an aqueous solution of a strong mineral acid, and the replacement of the halogen atoms Z is finally effected by hydroxyl groups; (c) when X<SP>1</SP> is a sulphur atom, reacting a mercaptoalkanoic acid or a salt or alkyl (of 1 to 6 carbon atoms) ester of such an acid with either an ether of glycidyl of the Formula (II): where R, X, A, A<SP>111</SP>, m and n are as defined above, or with an ether of allyl alcohol of the formula where R, X, A, A<SP>111</SP>, m and n are as defined above, and hydrolysis and/or saponification of the product obtained is thereafter optionally effected. The reaction employing the compound (II) is carried out at a temperature between 20‹ and 150‹ C. and as alkaline catalyst there may be used alkaline alcoholates, mercaptides, alkaline hydroxides or tertiary amines. The molar ratios of mercaptoalkanoic acid, of its salts or of its esters to the glycidyl ether employed are of the order of 1:1 to 1À5: 1 and preferably about 1: 1 to 1À1: 1.